Mild and Efficient Procedure for the Synthesis of 1,5‐Benzodiazepines Catalyzed by Magnesium Perchlorate

References

• Schutz , H. 1982 . Benzodiazepines Heidelberg , , Germany : Springer .
   Google Scholar
• Landquist , J. K. 1984 . In Comprehensive Heterocyclic Chemistry Edited by: Katritzky , A. R. and Rees , C. W. Vol. 1 , 166 – 170 . Oxford : Pergamon .
   Google Scholar
• Randall , L. O. and Kappel , B. 1973 . Benzodiazepines: Synthesis of Benzodiazepine Derivatives Edited by: Garattini , S. , Mussini , E. and Randall , L. O. 27 New York : Raven Press . and references cited therein
   Google Scholar
• Aversa , M. C. , Ferlazzo , A. , Giannetto , P. and Kohnke , F. H. 1986 . A convenient synthesis of novel [1,2,4]triazolo[4,3‐a][1,5]benzodiazepine derivatives . Synthesis , : 230 – 231 .
   Web of Science ®Google Scholar
• Essaber , M. , Baouid , A. , Hasnaoui , A. , Benharref , A. and Lavergne , J. P. 1998 . Synthesis of new tri‐ and tetraheterocyclic systems 1,3‐dipolar cycloaddition of nitrilimines on 2,7‐dimethyl‐4‐phenyl‐3H‐1,5‐benzodiazepine . Synth. Commun. , 28 : 4097 – 4104 .
   Web of Science ®Google Scholar
• El‐Sayed , A. M. , Abdel‐Ghany , H. and El‐Saghier , A. M. M. 1999 . A novel synthesis of pyrano(2,3‐c)‐, 1,3‐oxazino(2,3‐b)‐,1,2,4‐triazolo(3,4‐b)‐, oxazolo(2,3‐b)‐, furano(3,2‐c)‐ and 3‐substituted‐(1,5)benzodiazepine‐2‐ones . Synth. Commun. , 29 : 3561 – 3572 .
   Web of Science ®Google Scholar
• Reddy , K. V. V. , Rao , P. S. and Ashok , D. 2000 . Facile synthesis of 2‐benzoyl‐6‐hydroxy 3‐methyl‐5‐(2‐substituted‐2,3‐dihydro‐1H‐1,5‐benzodiazepine‐4‐yl)benzo[b]furans . Synth. Commun. , 30 : 1825 – 1836 .
   Web of Science ®Google Scholar
• Harris , R. C. and Straley , J. M. Cationic polymethine dyes for acrylic fibres . US Patent 1,537,757 . 1968 . Chem. Abstr. 1970, 73, 100,054w
   Google Scholar
• Grossi , G. , Di Braccio , M. , Roma , G. , Ballabeni , V. , Tognolni , M. , Calcina , F. and Barocelli , E. 2002 . 1,5‐Benzodiazepines, part XIII: Substituted 4H‐[1,2,4]triazolo[4,3‐a][1,5]benzodiazepin‐5‐amines and 4H‐imidazo[1,2‐a][1,5]benzodiazepine‐5‐amines as analgesic, anti‐inflammatory and/or antipyretic agents with low acute toxicity . Eur. J. Med. Chem. , 37 : 933 – 944 .
   PubMed Web of Science ®Google Scholar
• Kodomari , M. , Noguchi , T. and Aoyama , T. 2004 . Solvent‐free synthesis of 1,5‐benzothiazepines and benzodiazepines on inorganic supports . Synth. Commun. , 34 : 1783 – 1790 .
   Web of Science ®Google Scholar
• Reid , W. and Torinus , E. 1959 . Synthesis of condensed 5‐,7‐, and 8‐membered heterocycles with 2 nitrogen atoms . Chem. Ber. , 92 : 2902 – 2916 .
   Google Scholar
• Ma , Y. and Zhang , Y. 2002 . Derivatives of 2,3‐dihydro‐1H‐1,5‐benzodiazepine from o‐nitroanilines and chalcones induced by low‐valent titanium . Synth. Commun. , 32 : 165 – 169 .
   Web of Science ®Google Scholar
• Zhong , W. , Zhang , Y. and Chen , X. J. 2000 . Samarium diiodide mediated simultaneous reduction of nitro group and the azide group in o‐nitrophenylazide: A new access to 2,3‐dihydro‐1H‐1,5‐benzodiazepines . J. Chem. Res. (Synop.) , : 532 – 534 .
   Web of Science ®Google Scholar
• Herbert , J. A. L. and Suschitzky , H. 1974 . Synthesis of heterocyclic compounds, part XXIX: Substituted 2,3‐dihydro‐1H‐1,5‐benzodiazepines . J. Chem. Soc. Perkin Trans. 1 , : 2657 – 2661 .
   Google Scholar
• Morales , H. R. , Bulbarela , A. and Contreras , R. 1986 . New synthesis of dihydro‐ and terahydro‐1,5‐benzodiazepines by reductive condensation of o‐phenylenediamine and ketones in the presence of sodium borohydride . Heterocycles , 24 : 135 – 139 .
   Web of Science ®Google Scholar
• Jung , D. I. , Choi , T. W. , Kim , Y. Y. , Kim , I. S. , Park , Y. M. , Lee , Y. G. and Jung , D. H. 1999 . Synthesis of 1,5‐benzodiazepine derivatives . Synth. Commun. , 29 : 1941 – 1951 .
   Web of Science ®Google Scholar
• Balakrishna , M. S. and Kaboundin , B. 2001 . A simple and new method for the synthesis of 1,5‐benzodiazepine derivatives on a solid surface . Tetrahedron Lett. , 42 : 1127 – 1129 .
   Web of Science ®Google Scholar
• Kaboudin , B. and Kavaee , K. 2001 . Alumina/phosphorus pentoxide (APP) as an efficient reagent for the synthesis of 1,5‐benzodiazepines under microwave irradiation . Heterocycles , 55 : 1443 – 1446 .
   Web of Science ®Google Scholar
• Pozarentzi , M. , Stephanidou‐Stephanatou , J. and Tsoleridis , C. A. 2002 . An efficient method for the synthesis of 1,5‐benzodiazepine derivatives under microwave irradiation without solvent . Tetrahedron Lett. , 43 : 1755 – 1758 .
   Web of Science ®Google Scholar
• Reddy , B. M. and Sreekanth , P. M. 2003 . An efficient synthesis of 1,5‐benzodiazepine derivatives catalyzed by a solid superacid sulfated zirconia . Tetrahedron Lett. , 44 : 4447 – 4449 .
   Web of Science ®Google Scholar
• Yadav , J. S. , Reddy , B. V. S. , Eshwaraiah , B. and Anuradha , K. 2002 . Amberlyst‐15®: A novel and recyclable reagent for the synthesis of 1,5‐benzodiazepines in ionic liquids . Green Chem. , 4 : 592 – 594 .
   Web of Science ®Google Scholar
• Curini , M. , Epifano , F. , Marcotullio , M. C. and Rosati , O. 2001 . Ytterbium triflate promoted synthesis of 1,5‐benzodiazepine derivatives . Tetrahedron Lett. , 42 : 3193 – 3195 .
   Web of Science ®Google Scholar
• Luo , Y.‐Q. , Xu , F. , Han , X.‐Y. and Shen , X. 2005 . Samarium diiodide catalysed synthesis of 2,3‐dihydro‐1H‐benzo[b][1,4]‐diazepine derivatives . Chin. J. Chem. , 23 : 1417 – 1420 .
   Web of Science ®Google Scholar
• Yadav , J. S. , Reddy , B. V. S. , Satheesh , G. , Srinivasulu , G. and Kunwar , A. C. 2005 . InCl3‐catalyzed stereoselective synthesis of 1,5‐benzodiazepines . Arkivoc , iii : 221 – 227 .
   Web of Science ®Google Scholar
• Yadav , J. S. , Reddy , B. V. S. , Praveenkumar , S. and Nagaiah , K. 2005 . Indium(III) bromide: A novel and efficient reagent for the rapid synthesis of 1,5‐benzodiazepines under solvent‐free conditions . Synthesis , : 480 – 484 .
   Web of Science ®Google Scholar
• Sivamurugan , V. , Deepa , K. , Palanichamy , M. and Murugesan , V. 2004 . [(L)Proline]2Zn catalysed synthesis of 1,5‐benzodiazepine derivatives under solvent‐free conditions . Synth. Commun. , 34 : 3833 – 3846 .
   Web of Science ®Google Scholar
• Bandgar , B. P. , Bettigeri , S. V. and Joshi , N. S. 2004 . Molecular iodine catalyzed highly rapid synthesis of 1,5‐benzodiazepine derivatives under mild conditions . Synth. Commun. , 34 : 1447 – 1453 .
   Web of Science ®Google Scholar
• Chen , W.‐Y. and Lu , J. 2005 . Molecular‐iodine‐catalyzed one‐pot synthesis of 1,5‐benzodiazepine derivatives under solvent‐free conditions . Synlett , : 1337 – 1339 .
   Web of Science ®Google Scholar
• De , S. K. and Gibbs , R. A. 2005 . Scandium(III) triflate as an efficient and reusable catalyst for synthesis of 1,5‐benzodiazepine derivatives . Tetrahedron Lett. , 46 : 1811 – 1813 .
   Web of Science ®Google Scholar
• Sabitha , G. , Reddy , G. S. K. K. , Reddy , K. B. , Reddy , N. M. and Yadav , J. S. 2004 . A new, efficient and environmentally benign protocol for the synthesis of 1,5‐benzodiazepines using cerium(III) chloride/sodium iodide supported on silica gel . Adv. Synth. Catal. , 346 : 921 – 923 .
   Web of Science ®Google Scholar
• Chari , M. A. and Syamasundar , K. 2005 . Polymer (PVP) supported ferric chloride: An efficient and recyclable heterogeneous catalyst for high yield synthesis of 1,5‐benzodiazepine derivatives under solvent free conditions and microwave irradiation . Catal. Commun. , 6 : 67 – 70 .
   Web of Science ®Google Scholar
• Yadav , J. S. , Reddy , B. V. S. , Praveenkumar , S. , Nagaiah , K. , Lingaiah , N. and Saiprasad , P. S. 2004 . Ag3PW12O40: A novel and recyclable heteropoly acid for the synthesis of 1,5‐benzodiazepines under solvent‐free conditions . Synthesis , : 901 – 904 .
   Web of Science ®Google Scholar
• Jarikote , D. V. , Siddiqui , S. A. , Rajagopal , R. , Daniel , T. , Lahoti , R. J. and Srinivasan , K. V. 2003 . Room temperature ionic liquid promoted synthesis of 1,5‐benzodiazepine derivatives under ambient conditions . Tetrahedron Lett. , 44 : 1835 – 1838 .
   Web of Science ®Google Scholar
• Bartoli , G. , Bosco , M. , Locatelli , M. , Marcantoni , E. , Melchiorre , P. and Sambri , L. 2005 . Unusual and unexpected reactivity of t‐butyl dicarbonate (Boc2O) with alcohols in the presence of magnesium perchlorate: A new and general route to t‐butyl ethers . Org. Lett. , 7 : 427 – 430 .
   PubMed Web of Science ®Google Scholar
• Chakraborti , A. K. , Bhagat , S. and Rudrawar , S. 2004 . Magnesium perchlorate as an efficient catalyst for the synthesis of imines and phenylhydrazones . Tetrahedron Lett. , 45 : 7641 – 7644 .
   Web of Science ®Google Scholar
• Chen , W.‐Y. and Liu , J. 2004 . Mg(ClO4)2 as a powerful catalyst for synthesis of 1,2,3,4‐tetrahydropyrimidin‐2‐ones . Chin. J. Org. Chem. , 24 : 1111 – 1113 .
   Web of Science ®Google Scholar
• Bandgar , B. P. , Kamble , V. T. and Bavikar , S. N. 2003 . Magnesium perchlorate: An efficient catalyst for selective sulfonylation of arenes under neutral conditions . J. Chem. Res. (Synop.) , : 287 – 289 .
   Google Scholar
• Bartoli , G. , Bosco , M. , Dalpozzo , R. , Marcantoni , E. , Massacesi , M. , Rinaldi , S. and Sambri , L. 2003 . Mg(ClO4)2 as a powerful catalyst for the acylation of alcohols under solvent‐free conditions . Synlett , : 39 – 42 .
   Web of Science ®Google Scholar
• Yang , D. , Yan , Y.‐L. and Bob , L. 2002 . Mild α‐halogenation reactions of 1,3‐dicarbonyl compounds catalyzed by Lewis acids . J. Org. Chem. , 67 : 7429 – 7431 .
   PubMed Web of Science ®Google Scholar
• Gooßen , L. and Döhring , A. 2003 . Lewis acids as highly efficient catalysts for the decarboxylative esterification of carboxylic acids with dialkyl dicarbonates . Adv. Synth. Catal. , 345 : 943 – 947 .
   Web of Science ®Google Scholar
• Zhang , Z.‐H. 2004 . Indium tribromide/[bmim]PF6: A novel and recyclable catalytic system for the deprotection of 1,1‐diacetates . J. Chem. Res. (Synop.) , : 753 – 755 .
   Google Scholar
• Zhang , Z.‐H. 2005 . Sodium hydrogen sulfate in poly(ethylene glycol): An efficient recyclable system for the deprotection of 1,1‐diacetates . Monatsh. Chem. , 136 : 1191 – 1195 .
   Web of Science ®Google Scholar
• Mo , L.‐P. , Ma , Z.‐C. and Zhang , Z.‐H. 2005 . CuBr2‐catalyzed synthesis of bis(indolyl)methanes . Synth. Commun. , 35 : 1997 – 2004 .
   Web of Science ®Google Scholar